• I'm grateful to my grandmother for raising me, but my childhood was lonely. 
• I thought I'd embrace being alone as an adult, but instead, I've filled my life with love.
• My wife and I have chosen to be child-free. We're intentional about connections with chosen family.

I´m in my 30s, but I joke that I´ve been a grandma since birth. I'm an only child, and my grandmother raised me while my parents were out of the picture. I grew up in a sleepy town built around fishermen and summer tourists. My grandmother's house was on a peninsula, a seven-mile stretch of the Atlantic on the south shore of Massachusetts.

My grandmother was my world, and I understood from a young age that I was lucky to live with her; grandparents aren't obligated to raise their child´s child, and if it weren't for her willingness to act as my guardian, I´m not sure what would have become of me.

But I still envied my peers with siblings or close cousins; I'd walk the beach with my grandma and long to join kids who were learning to surf with their parents or playing volleyball as a family, activities my aging grandmother simply couldn't keep up with.

I´ve always had poor eyesight and often became clingy and afraid without my glasses. I'd never been able to see my grandmother from the water and dreaded seeing her become a blurry speck on shore. I remember her best up close: big dark eyes, small stature, knuckles gnarled from arthritis.

I felt safer right beside her, where I could see her clearly and trust she wouldn´t simply disappear, but I knew better than to ask her to swim with me; she wore slacks and blouses to the beach for a reason. She raised six children, then me — I understood she was fragile, and that I was lucky to live with her during her golden years.

She often told me, "My body doesn't recover like yours," and encouraged me to do scary things on my own, like search for shells underwater and say hi to strangers.

I was lonely in childhood, but I still choose to be child-free

I didn't much enjoy childhood, but as a child-free adult by choice, I'm embracing the freedom being childless gives me with the support of my chosen family. Since moving from my grandmother's home more than a decade ago — first to New York, then Boston, then DC, then Atlanta, then Seattle, and now an island in the Caribbean — I´ve greeted many strangers and felt both lonely and beloved.

Since her death eight years ago, I've traveled the world like my grandmother never got to — taken solo trips to Iceland for all-night sunshine, gone to Montreal for Pride, and recently, visited the French Alps to spend time with a friend and her wife — and even saved up for corrective eye surgery, hoping Lasik would make me braver, as well as more sporty and spontaneous.

After Lasik, I did become braver — I joined strangers to go hiking, signed myself and my wife up for snowshoeing, and went camping with girls I knew from the internet. I felt less nerdy, less the shy girl hiding behind a book (though I did, and do, always carry a book with me). It's taken a return to the Atlantic, where my wife and I live for her job, to realize what I don't need is to simply see clearly, but to trust I have people looking out for me.

We fill our lives with the love of our friends

My wife and I are firm on our decision not to have children, but after moving cross-country for work repeatedly, we´ve come to love hosting people at our home to build memories.

My friend and her wife came to visit us from France, bringing with them a penchant for home cooking and tips on how to air-dry clothes. We snorkeled, swam, and spent long hours exploring the island. I fretted about nature cooperating, but my friend just reassured me they came to spend time with me — she doesn't even like the heat!

Our friends are already planning to come back and stay with us again, creating new memories and traditions. They even discussed the logistics of bringing a future child and talked about names and parenting values.

I hoped I'd have shaken the chronic loneliness of my childhood by the time I became an adult and learned to embrace being alone without feeling alone, but instead, I'm giving myself the company I always longed for.

Over the years, I've joined a queer bowling league, played bingo orchestrated by drag queens, and dragged my wife to board game nights. Growing up, I was jealous of kids who had siblings because at least they had someone as a built-in companion, but nurturing friendships in adulthood is teaching me the value of a small but earnest circle. It's not about having people beside me, as I once envied, but about people who will forge the distance, even when it's a plane ride away.

Watching my friends excitedly become parents affirms my decision not to. It could be tempting to have kids to facilitate the childhood I didn't have, filled with siblings and active parents, but parenting to heal childhood wounds feels misguided and puts the onus on a child who didn't ask to be here. I also don't trust myself to teach someone about the world when I´ve barely figured it out myself.

My younger self wouldn't believe I´m not only openly gay but married, and she especially wouldn't believe I have people looking out for me, even when they're out of sight.

• Larry Ellison, the 79-year-old cofounder of Oracle, is one of the most interesting men in tech.
• Whether yacht racing, buying Hawaiian islands, or trash-talking competitors, he keeps it lively.
• Now, he's one of the world's richest people with a net worth of about $152 billion.

Larry Ellison is the founder and chief technology officer at software company Oracle. Now, he's also the world's seventh richest man and has a net worth of $152 billion, according to the Bloomberg Billionaires Index.

The billionaire's fortunes have surged by $14 billion thanks to spiking demand for generative AI. The windfall puts him ahead of tech execs like Google cofounder Sergey Brin and former Microsoft chief executive Steve Ballmer. 

The 79-year-old started Oracle in 1977, and decades later he's still one of the top dogs in Silicon Valley despite living in Hawaii full time — and owning an entire island. Ellison has also been a major investor in Tesla, Salesforce, and even reportedly had a seat on Apple's board of directors for a while.

Outside the office, the billionaire boasts an impressive watch collection and indulges in hobbies like yacht racing.

Here's a look at the life and career of Ellison so far.

Lawrence Joseph Ellison was born in the Bronx on August 17, 1944, the son of a single mother named Florence Spellman.

When he was 9 months old, Larry came down with pneumonia, Vanity Fair reported. His mom sent him to Chicago to live with his aunt and uncle, Lillian and Louis Ellison.

Vanity Fair reported that Louis, his adoptive father, was a Russian immigrant who took the name "Ellison" in tribute to the place in which he entered the US: Ellis Island.

Ellison is a college dropout.

Ellison went to high school in Chicago's South Side before attending the University of Illinois at Urbana-Champaign. When his adoptive mother died during his second year at college, Ellison dropped out. He tried college again later at the University of Chicago but dropped out again after only one semester, Vanity Fair reported.

In 1966, a 22-year-old Ellison moved to Berkeley, California — near what would become Silicon Valley and already the place where the tech industry was taking off.

He made the trip from Chicago to California in a flashy turquoise Thunderbird that he thought would make an impression in his new life, Vanity Fair reported.

Ellison bounced around from job to job, including stints at companies like Wells Fargo and the mainframe manufacturer Amdahl. Along the way, he learned computer and programming skills.

In 1977, Ellison and partners Bob Miner and Ed Oates founded a new company, Software Development Laboratories.

The company started with $2,000 of funding.

Ellison and company were inspired by IBM computer scientist Edgar F. Codd's theories for a so-called relational database — a way for computer systems to store and access information, Britannican said. Nowadays, they're taken for granted, but in the '70s, they were a revolutionary idea.

The first version of the Oracle database was version 2 — there was no version 1.

In 1979, the company renamed itself Relational Software Inc., and in 1982, it formally became Oracle Systems Corp., after its flagship product.

In 1986, Oracle had its initial public offering, reporting revenue of $55 million.

As one of the key drivers of the growing computer industry, Oracle grew fast. The company is responsible for providing the databases in which businesses track information that is crucial to their operations.

Ellison became a billionaire at age 49. Now, he has a net worth of roughly $152 billion, according to Forbes, after racking up $50 billion in gains thanks to Oracle and Tesla stock. That makes him the seventh-richest person in the world.

Still, in 1990, Oracle had to lay off 10% of its workforce, about 400 people, because of what Ellison later described as "an incredible business mistake."

Oracle reported a loss of $36 million in September 1990 after admitting that it had miscalculated its revenue earlier that year, The New York Times reported.

It didn't get the decade off to a great start. After adjusting for that error, Oracle was said to be close to bankruptcy. At the same time, rivals like Sybase were eating away at Oracle's market share.

It took a few years, but by 1992, Ellison and Oracle managed to right the course with new employees and the popular Oracle7 database.

Ellison is known for his willingness to trash-talk competitors.

For much of the '90s, he and Oracle were locked in a public-relations battle with the competitor Informix, which went so far as to place a "Dinosaur Crossing" billboard outside Oracle's Silicon Valley offices at one point, Fortune reported in 1997.

His financial success has led to some expensive hobbies.

With Ellison as Oracle's major shareholder, his millions kept rolling in. He started to indulge in some expensive hobbies — including yacht racing. That's Ellison at the helm during a 1995 race.

He also partly financed the BMW Oracle USA sailing team, which won the America's Cup in 2010, according to Bloomberg.

Ellison was an early investor in Salesforce.

In 1999, Ellison's protégé, Marc Benioff, left Oracle to work on a new startup called Salesforce.com. Ellison was an early investor, putting $2 million into his friend's new venture.

When Benioff found out that Ellison had Oracle working on a direct competitor to Salesforce's product, he tried to force his mentor to quit Salesforce's board. Instead, Ellison forced Benioff to fire him — meaning Ellison kept his shares in Salesforce.

Given that Salesforce is now a $267 billion company, Ellison personally profits even when his competitors do well. It has led to a love-hate relationship between the two executives that continues to this day, with the two taking shots at each other in the press.

The dot-com boom of the late '90s benefited Oracle.

All of those new dot-com companies needed databases, and Oracle was there to sell them. Although investors lost out in the dot-com crash, Oracle came out of it stronger due to its acquisitions and the demand for software solutions.

With the coffers overflowing, Ellison was able to lead Oracle through a spending spree once the dot-com boom was over and prices were low.

In 2005, for example, Oracle snapped up the HR software provider PeopleSoft for $10.3 billion.

And in 2010, Oracle completed its acquisition of Sun Microsystems, a server company that started at about the same time as Oracle, in 1982. That acquisition gave Oracle lots of key technology, including control over the popular MySQL database.

Ellison has also spent lavishly over the years, so much so that his accountant, Philip Simon, once asked him to "budget and plan," according to Bloomberg.

Ellison has expensive taste. Over the years he's built up an impressive collection of Richard Mille watches, an expert previously told BI. The timepieces start in the six-figure range and can go for over $1 million in some cases.

In 2009, the billionaire purchased the Indian Wells tennis tournament for a reported $100 million, The Los Angeles Times reported.

In 2010, Ellison signed the Giving Pledge.

By signing the pledge, Ellison promised to donate 95% of his fortune before he dies. And in May 2016, Ellison donated $200 million to a cancer treatment center at the University of Southern California, Forbes reported.

Starting in the 2010s, Ellison started to take more of a back seat at Oracle, handing more responsibilities to trusted lieutenants, like Mark Hurd and Safra Catz, then Oracle's copresidents.

Ellison hired Hurd, a former CEO of HP, in 2010, Inc reported. Catz has made a reputation for herself among analysts for what they describe as brilliant business strategy.

But Ellison's spending didn't slow down. In 2012, he bought 98% of the Hawaiian island of Lanai.

Ellison founded a startup called Sensei in 2016 that does hydroponic farming and owns a wellness retreat on Lanai.

He also purchased Hawaiian budget airline Island Air in 2014, before selling a controlling interest in the airline two years later after it struggled financially.

In 2014, Ellison officially stepped down as Oracle CEO.

Ellison handed control over to Hurd and Catz, who became co-CEOs. Ellison now serves as the company's chairman and chief technology officer. Following Hurd's death in 2019, Catz became the sole CEO.

In 2016, Ellison scored a personal coup: the purchase of NetSuite.

Back in 1998, Ellison had made a $125 million investment in ex-Oracle exec Evan Goldberg's startup business-management software firm, NetSuite. It ended up working out well for Ellison when NetSuite CEO Zach Nelson negotiated the sale of the company to Oracle for $9.3 billion, netting Ellison a cool $3.5 billion in cash for his stake.

NetSuite investor T. Rowe Price tried to block the deal, citing Ellison's conflict of interest, but the sale closed in November 2016.

He's used his billions in a variety of ways: he invested in educational platform maker Leapfrog Enterprises and was an early investor in the ill-fated blood-testing company Theranos.

Ellison has held shares in some of the most recognizable companies, one of which was the infamous blood-testing company Theranos, founded by Elizabeth Holmes. It had a promising future until its flaws were exposed and Holmes received a prison sentence.

When Steve Jobs returned to Apple as CEO back in 1997, he asked Ellison to sit on the board. Ellison served for a while, but felt that he couldn't devote the time and left in 2002, according to Forbes. Compensation for his role was an option to buy about 70,000 shares, which would've amounted to about $1 million at the time of his departure.

Ellison owns homes on the East and West coasts as part of a multibillion-dollar real-estate portfolio.

Ellison reportedly owns the Astor Beechwood Mansion in Newport, Rhode Island, and a home in Malibu. Ellison also has houses in Palm Beach, Florida and more in a multibillion-dollar real-estate portfolio.

Both of his two children work in the film industry.

His daughter, Megan, is an Oscar-nominated film producer and the founder of Annapurna Pictures. The company has produced films like "Zero Dark Thirty" and "American Hustle."

Ellison's son, David, is also in the film business. His company, Skydance Media, has produced movies like "Terminator: Dark Fate" and films in the "Mission: Impossible" franchise. Whispers of David becoming the new owner of Paramount swirled in April due to his father's net worth.

Ellison has a reputation as an international, jet-setting playboy.

Ellison has been married and divorced four times. He's most recently dated Nikita Kahn, a model and actress.

Ellison was one of the few tech leaders who had a friendly relationship with former President Donald Trump.

Ellison said publicly that he supported Trump and wants him to do well, and hosted a Trump fundraiser at his Rancho Mirage home in February, though he did not attend. The fundraiser caused an outcry among Oracle employees, who started a petition asking senior Oracle leadership to stand up to Ellison.

Catz, the CEO of Oracle, also had close ties to the Trump administration, having served on Trump's transition team. 

Ellison and Trump remained close during Trump's time in office and reportedly spoke on the phone about possible coronavirus treatments. Trump also supported Oracle's bid to buy TikTok, calling Oracle a "great company."

In December 2018, Ellison joined the board of directors at Tesla, where he's been a major investor.

Earlier in 2018, Ellison described Tesla CEO Elon Musk as a "close friend," and defended him from critics. When Musk acquired Twitter — now X — in 2022, Ellison offered to invest $1 billion.

Musk went on to help Ellison reset his forgotten password, biographer Walter Isaacson wrote.

In December 2020, Ellison revealed that he moved to Lanai full-time.

The announcement came after Oracle decided to move its headquarters to Austin, leading Oracle employees to ask Ellison if he planned to move to Texas too.

"The answer is no," Ellison wrote in a company-wide email. "I've moved to the state of Hawaii and I'll be using the power of Zoom to work from the island of Lanai."

He signed the email: "Mahalo, Larry."

He left Tesla's board in August 2022.

In a proxy filing in June 2022, the electric vehicle maker revealed that Ellison would be leaving the board. Since then, he and Musk have appeared to maintain their close relationship.

Oracle had a record-breaking 2023, and cemented itself in the new age of artificial intelligence.

Oracle's shares continued to hit records, CNBC reported. The company proved that it's not going any where any time soon.

In 2023, Oracle backed OpenAI rival Cohere.

Oracle joined other tech giants, like Salesforce, in backing the tech startup in June 2023. It began offering generative AI to its clients based on tech made by Cohere.

"Cohere and Oracle are working together to make it very, very easy for enterprise customers to train their own specialized large language models while protecting the privacy of their training data," Ellison previously said.

Oracle announced in April that it would be moving its headquarters to Nashville, Tennessee.

Despite its big move to Austin only four years ago, Ellison said that Oracle is planning to move its world headquarters to Nashville, Tennessee.

In April 2024, the exec announced that Oracle has plans for a "huge campus" in Nashville that will one day serve as the software giant's world headquarters. The company relocated from the San Francisco area to Austin, Texas in 2020.

"It's the center of the industry we're most concerned about, which is the healthcare industry," Ellison said at the Oracle Health Summit in Nashville, CNBC reported.

Matt Weinberger and Taylor Nicole Rogers contributed to an earlier version of this story.

Correction: May 7, 2024 — An earlier version of this story misstated Larry Ellison's role at Oracle. He's the chief technology officer, not the CEO.

Ellison's wealth jumped $14 billion after record earnings from Oracle.

Oracle's cloud applications business saw its shares spike by 13% in June 2024 after the company posted strong annual earnings due to demand for generative AI, Fortune reported. Ellison, who now serves as Oracle's CTO and owns about 40% of the company's cloud sector, got a $14 billion boost to his fortune.

The company also announced a partnership with AI startup Cohere, enabling its enterprise customers to build their own generative AI apps. "Cohere and Oracle are working together to make it very, very easy for enterprise customers to train their own specialized large language models while protecting the privacy of their training data," Ellison said during the company's earnings call.

• Tesla announced investors approved Elon Musk's pay package.
• The package, initially approved in 2018, was voided by a Delaware judge in January.
• Tesla is hoping the shareholder ratification will make the judge's ruling moot, but it's not guaranteed.

It's official — Tesla investors voted to approve Elon Musk's pay package.

The carmaker announced the results of the shareholder vote during the company's annual meeting on Thursday.

Investors had initially approved the compensation plan in 2018, but a Delaware judge voided it in January after a shareholder filed a lawsuit alleging the agreement was "beyond the bounds of reasonable judgment."

In January, Delaware Chancellor Kathaleen McCormick said she had decided to strike down the pay package because she believed Musk had undue influence over the agreement and its approval due to his close ties to several board members, one of which is his brother.

Tesla has yet to appeal the decision, but the company hopes to use the shareholder approval to argue that the ruling is moot now — the question now is whether the Delaware court will agree. The company said in a filing with the Securities and Exchange Commission on Monday that it will seek to reverse the ruling and will use an affirmative vote to do so.

When the compensation package was voided, it was estimated to be worth around $55 billion — making it the largest pay package to ever be awarded to a CEO.

Musk does not receive a salary from Tesla. His pay was determined by his ability to hit a series of financial goalposts. It consists of a 10-year grant comprising 12 sets of stock options. These options become available to Musk when Tesla achieves the specific goals. Each time a milestone is met, Musk receives stock equivalent to 1% of Tesla's outstanding shares at the time of the grant. By 2023, Tesla said it had successfully reached all 12 milestones.

Tesla has argued that the pay package is both fair and necessary to maintain Musk's focus on the car company. And the company went all out in its efforts to promote Musk's pay package, paying for advertisements and even offering shareholders who voted a chance to win a tour of the Texas gigafactory alongside Musk.

Some Tesla fans took to social media to promote the proposal, joining with some of the company's notable shareholders, such as Ron Baron of Baron Funds and Cathie Wood of Ark Investment Management, who were quick to rally around Musk.

"Elon is the ultimate 'key man' of key man risk. Without his relentless drive and uncompromising standards, there would be no Tesla," Baron wrote in an open letter last week.

One big reason investors are rallying around Musk: they are afraid of losing him — or at least his attention. The CEO has threatened to take his plans for AI and robotics elsewhere, saying that unless he had about 25% of voting control, he would "prefer to build products outside of Tesla."

"He is putting a knife at the throat of the company: 'You don't pay me what I want, then I am going to compete,'" Anat Alon-Beck, a corporate law expert at Case Western Reserve University, told BI.

During the annual meeting, Tesla announced that a proposal to move Tesla's state of incorporation to Texas had been approved. Earlier this year, Musk moved SpaceX's state of incorporation from Delaware to Texas as well.

Additionally, shareholders approved a proposal to reelect Tesla board members Kimbal Musk and James Murdoch.

This is a developing story. Check back for updates.

Do you work for Tesla or have a tip? Reach out to the reporter via a non-work email and device at gkay@businessinsider.com or 248-894-6012.

• Kate Winslet says filming the "I'm flying" scene in "Titanic" was a "nightmare."
• The iconic scene required four reshoots due to lighting and makeup issues.
• "Every young girl in the world wanted to be kissed by Leonardo DiCaprio," Winslet told Vanity Fair. "It was not all it's cracked up to be."

In a film full of memorable scenes, there's one in James Cameron's 1997 epic "Titanic" that stands out for its pure romance: The "I'm flying" scene, in which Kate Winslet's Rose and Leonardo DiCaprio's Jack share a passionate kiss on the ship's bow as the Céline Dion song "My Heart Will Go On" plays in the background.

But in reality, the scene was a nightmare to film. At least, according to Kate Winslet.

"My god, he's quite the romancer, isn't he? No wonder every young girl in the world wanted to be kissed by Leonardo DiCaprio," Winslet said while rewatching the scene for Vanity Fair. "It was not all it's cracked up to be."

Winslet said that Cameron wanted a specific light for the scene, and it kept changing on them. On top of that, there was no way for hair and makeup to do touch-ups on the actors between shots because of where they were standing, so Winslet had to do both their makeup and hide their brushes inside her corset.

"We kept doing this kiss, and I've got a lot of pale makeup on and I would have to do our makeup checks — on both of us, between takes — and I would end up looking as though I'd been sucking a caramel chocolate bar after each take because his makeup would come off on me."

DiCaprio, who had fake tan makeup on, looked like "there was a bit missing from his face" after each take, Winslet said. "Oh God, it was such a mess."

Despite all that, the finished received much acclaim. "Titanic" went on to win 11 Oscars, including best picture and best director for Cameron. It was the highest-grossing movie ever until Cameron made "Avatar" in 2009.

"I do feel very proud of it because I feel that it is that film that just keeps giving," Winslet said of "Titanic." "Whole other generations of people are discovering the film or seeing it for the first time, and there's something extraordinary about that."

Of course, that means every time Winslet is on a boat, people try to get her to reenact the "I'm flying" scene.

Does she agree to do it?

"Sometimes yes, sometimes no," she said.

Anthony Michael Hall has spent most of his life in front of the camera, and he has the stories to prove it.

Some of them are downright enviable. He hung out with comedy legends Chevy Chase and John Candy while filming his first starring role in "National Lampoon's Vacation," became the muse of 1980s auteur John Hughes with "The Breakfast Club" and "Sixteen Candles," and was the youngest "Saturday Night Live" cast member ever after joining the show at 17.

But some of them are less so. Hall's 1986 film "Out of Bounds," his attempt at becoming a dramatic leading man, was a flop. He was part of what's regarded as one of the worst "Saturday Night Live" seasons of all time. Hard-partying forced him to step away from Hollywood.

It's enough stories for a lifetime — and all of that happened by his mid-20s.

Now 56 and with the dreaded transition from teen star to adult actor decades behind him, Hall has added many more memorable roles to his credits: he played Bill Gates in the 1999 TV movie "Pirates of Silicon Valley," popped up in Christopher Nolan's "The Dark Knight," and went toe-to-toe with Michael Myers in "Halloween Kills." Soon, he'll add another to the list: a sleazy politician who gets on Jessica Alba's bad side in the Netflix action movie "Trigger Warning," out June 21.

For the latest interview in Business Insider's "Role Play" series, Hall opens up about his partying days, why he turned down the lead role in Stanley Kubrick's "Full Metal Jacket," and his plan to make a "Succession"-like comedy series with his good friend Robert Downey Jr.

On hitting puberty during reshoots of 'National Lampoon's Vacation' and meeting John Candy

"National Lampoon's Vacation" was your first movie, and the ending was reshot. As a kid, was it strange to do a reshoot?

We did the reshoot for "Vacation" six or nine months later. The funny thing is that puberty had fully kicked in for me. I'm literally seven inches taller. So if you look at the movie closely, you'll see that my hair is darker, and I got taller and skinnier. The first day on set for the reshoot, I see Chevy, and he sees that I have one or two giant pimples, and he goes, "If you're going blind, you're doing it right." He was just messing with me because, seeing how I looked, he guessed I had started masturbating. Chevy was like that. 

And the other thing was I learned John Candy was going to be part of the reshoots. I used to watch "SCTV," so I loved him, and one of the sketches he used to do was the Schmenge brothers with Eugene Levy, they were Polish variety show hosts. So I brought that to John's attention, and he said, "We're going to make you an honorary Schmenge, Michael," he would talk to me like his Schmenge character. That's how cool he was. He really was like Uncle Buck. 

On doing 10 auditions for 'Sixteen Candles' and casting John Cusack himself

Is it true you did 10 auditions for the Ted role in "Sixteen Candles"?

I think so. It was in that range. 

Was John Hughes at all of them?

I believe he was at all of them. As well as Jackie Burch, the casting director. But the thing was that with every successive round of audition, they would add more executives from the studio showing up. 

So you would feel good if the room filled up more and more.

Exactly. I felt I was getting closer to landing the job because they kept asking me to come back and do the same scenes, and there would be more and more people. 

Do you think you and John clicked through that process, or was it not until filming started?

I think it was actually through the audition. Because I felt like he was rooting for me. 

Is it true that you were the one who cast John Cusack for the role of Bryce, one of Ted's geek friends?

Yes. And that was at John Hughes' direction. He literally said that to me one day. He said, "They are going to be your buddies in the movie, so I want you to cast them." I was stunned. I was a 15-year-old kid. I couldn't believe he said that. So I cast John and Darren Harris. 

By the time "The Breakfast Club" came out, you were one of the biggest teen stars in Hollywood. What was that like for you?

I was excited and stunned. I think when it started to kick in for me was even before that, it was when we had screenings of "Sixteen Candles." I remember John was doing post-production on "Sixteen Candles," and he wanted to show it to me. I went to the Waldorf Astoria with my father to see John, and he showed it to us on VHS in his beautiful penthouse suite. I remember tripping out because I was watching the movie, and I really laughed and thought it was funny. That marks the beginning of when I felt something was starting for me. 

By the time "The Breakfast Club" came around, he had called me at home. This is six or eight months later because he did "Sixteen Candles," "The Breakfast Club," and "Weird Science" consecutively. My parents gave me the phone, and he just told me about the movie and my part, and that's how I got involved with that. We would always call each other and talk over the phone, just as friends. 

On wild nights out while making 'Weird Science' and starring on 'SNL' simultaneously

We have to talk about 1984 to 1986 because that is a defining moment in your life and career. You were on "Saturday Night Live" as the youngest cast member ever at 17 years old. You were finishing up "Weird Science," and were looking to do your first dramatic role with "Out of Bounds" after declining to play the lead in Hughes' "Ferris Bueller's Day Off."

You were living in the Chateau Marmont with a giant billboard of "Weird Science" right outside your window. You were flying back to New York weekly for "SNL." And, on either coast, you were partying with the likes of Robert Downey Jr. and Mike Tyson. What the heck was life like for you then?

Dude, it's like you were there the way you just described that! That was startling. No, it was incredible for me. I remember taking a meeting to do "Out of Bounds," and at that point, I felt personally I was riding the crest of these three John Hughes movies, and I was loving it, but part of me wanted to move forward, and that's why I chose that film. It was a chance to step in a new direction after three comedies. And, yes, I was going back and forth to New York to do "SNL" because my deal for the 1985 season was not like the other cast members — I only did like 13 or 14 episodes while everyone else did 20-22. It was a whirlwind. 

A whirlwind for sure. Looking back, did you burn both ends of the candle?

It was a lot to deal with, absolutely. And we're talking about the age of 15 to 20. I'd done all those films and "SNL," and truthfully, yeah, those were my partying days. I grew up in Manhattan, so it wasn't something I had to reach for. It was always right there. I certainly had my wild nights. But I feel by the time I was in my mid-20s it shifted because I had to reinvest in my craft and take it seriously and rebuild. 

On his biggest career regret and working with Tim Burton on 'Edward Scissorhands'

I have to bring up one more thing from this time span: Stanley Kubrick calls you to play the lead in "Full Metal Jacket."

Oh, shit. Yeah.

Is it true that there was a nine-month negotiating period to determine whether you were going to sign on for the role of Joker?

That's right. 

But set the record straight, because you have said different things over the years: Did you walk away because of the money being offered, or was it the character and the amount of time you'd have to dedicate to the role?

Here's the thing: I remember I had to go to Kubrick's lawyer's house, who lived in the Bel Air section of Beverly Hills. I was with my father. He escorted me into his kitchen, and I sat down and read a script that was numbered because Kubrick was extremely private, and I read "Full Metal Jacket." But it was such a long and drawn-out process. At one point, I remember the lawyer calling my father, and Kubrick had a question for my father; he wanted to know if he had read a book called "Nuclear Negotiations," because that's how long these talks were going. 

But to answer your question, and it's a good one, I think it was about not just the money but what it represented. He really wasn't giving me a legitimate deal. And because I did my research, I knew that I'd be working for a year on that movie. In fact, I happened to run into Matthew Modine a year and a half later, and I asked him, "How long did you guys shoot?" And he was like, "54 weeks." 

So it was about the money. We couldn't come to an agreement on the deal and that's ultimately why I walked away. If I have anything close to a regret in my career, it would be not doing that movie. But I'm not a person who lives with regret, so I feel I grew from that experience. And I wound up having a conversation with him after all that. 

With Kubrick?

Yeah. It was really interesting. He basically told me he had a lot of budgetary restraints, and I talked to him about that. Unfortunately, it didn't work out, but I was able to have two conversations with the man: at the beginning, when he offered me the role and he talked about his influences like Chaplin and Russian films, and then at the end. The whole thing was an interesting experience. 

You took some time off after "Out of Bounds" and reemerged as the bully Jim in Tim Burton's "Edward Scissorhands." Was it a confidence boost for you when that movie became a hit?

It totally was. I remember I got a meeting in New York with Tim. I was super stoked to see him. A modern-day Walt Disney. He was super laid back at the meeting. He was soft-spoken and really chill. And I was in my early 20s by then and had another growth spurt, so I think he loved that coming off the John Hughes movies and people knowing me as the geek from those, he thought it would be interesting to cast me in that Jim role. Basically, to go against type. 

We shot in the Tampa area. I'll never forget: I went into his office, and he had all the drawings for "The Nightmare Before Christmas" on the wall. So he was thinking about that even though he was in production on "Scissorhands." And he would come so alive once he was on set. He's so calm and reserved, but on set, a switch flips and he comes to life. 

On Christopher Nolan's on-set uniform and developing a 'Succession'-like TV series with Robert Downey Jr.

You have worked with many greats. How do you compare Christopher Nolan when you worked with him on "The Dark Night"?

He's up there. Hughes. Burton. Nolan, I love, too. With the scale and the scope of the movie, I always just went with what was on the page; I never tried to improvise. I remember on set, he always wore the same thing: jeans, a vest, and a lengthy jacket. He looked like a conductor. He had a uniform, it seemed. He was kind of like a pied piper because, with every shot, there would be a trail of four or five people behind him.

I heard you and Robert Downey Jr. developing something together.

We are. I can tell you that we are in development; it's been years. We wrote a TV series together, we're calling it "Singularity," and it's based on an idea Downey had. It's taken a while because, at a certain point, we had to change things because it wound up being too similar to "Succession." What I mean by that is I would have played one of three sons, and the father was this tycoon industrialist. It's more of a comedic tone than "Succession," but it mirrored it too much, so we had to change things. Downey and I actually had a Zoom session the other day with a top producer who will hopefully come on board. 

Would Downey be on camera alongside you?

He is willing to do that. He might direct the pilot and some other episodes along with being in it. 

Would you direct some episodes? 

I would love to. This is really Downey's idea, so he's committed to being a part of it. 

You've had so many different eras of your career. Is there anything else you still want to try?

Writer-director. I've written something that I really want to make. I would star and direct it. It has been a passion and desire for me to do that for many years now. It's the next evolution in my career, being behind the camera. 

This interview has been edited and condensed for clarity.